US9738644B2 - Chemical compounds, compositions and methods for kinase modulation - Google Patents
Chemical compounds, compositions and methods for kinase modulation Download PDFInfo
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- US9738644B2 US9738644B2 US14/869,637 US201514869637A US9738644B2 US 9738644 B2 US9738644 B2 US 9738644B2 US 201514869637 A US201514869637 A US 201514869637A US 9738644 B2 US9738644 B2 US 9738644B2
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- alkyl
- heteroaryl
- substituted
- cancer
- cycloalkyl
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- UOFXHFRBDAUENE-HNNXBMFYSA-N C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(C3=CN(C)N=C3)=C2C(=O)N1C1=CC(F)=CC=C1 Chemical compound C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(C3=CN(C)N=C3)=C2C(=O)N1C1=CC(F)=CC=C1 UOFXHFRBDAUENE-HNNXBMFYSA-N 0.000 description 1
- YADQKTMILULBSD-LBPRGKRZSA-N C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(C3=CN=CC=C3)=C2C(=O)N1 Chemical compound C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(C3=CN=CC=C3)=C2C(=O)N1 YADQKTMILULBSD-LBPRGKRZSA-N 0.000 description 1
- AAKXBEVPFWYZQD-INIZCTEOSA-N C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(N3C=CC=N3)=C2C(=O)N1C1=CC=CC=C1 Chemical compound C[C@H](NC1=NC=NC2=C1N=CN2)C1=CC2=CC=CC(N3C=CC=N3)=C2C(=O)N1C1=CC=CC=C1 AAKXBEVPFWYZQD-INIZCTEOSA-N 0.000 description 1
- ACPVQRYVOACOJT-KRWDZBQOSA-N C[C@H](NC1=NC=NN2C=NC=C12)C1=CC2=CC=CC(C3=CN(C)N=C3)=C2C(=O)N1C1=CC=CC=C1 Chemical compound C[C@H](NC1=NC=NN2C=NC=C12)C1=CC2=CC=CC(C3=CN(C)N=C3)=C2C(=O)N1C1=CC=CC=C1 ACPVQRYVOACOJT-KRWDZBQOSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N C[n]1nccc1 Chemical compound C[n]1nccc1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- QMKNTHBESSANCI-JVUOZDSTSA-N ClC1=C2C(Br)=CNC2=NC=N1.ClC1=C2C=CNC2=NC=N1.N#CC1=CNC2=NC=NC(Cl)=C12.O/N=C\C1=CNC2=NC=NC(Cl)=C12.O=CC1=CNC2=NC=NC(Cl)=C12 Chemical compound ClC1=C2C(Br)=CNC2=NC=N1.ClC1=C2C=CNC2=NC=N1.N#CC1=CNC2=NC=NC(Cl)=C12.O/N=C\C1=CNC2=NC=NC(Cl)=C12.O=CC1=CNC2=NC=NC(Cl)=C12 QMKNTHBESSANCI-JVUOZDSTSA-N 0.000 description 1
- OVSFACADZSVZKO-UHFFFAOYSA-N ClC1=C2C(Br)=CNC2=NC=N1.NC(=O)C1=CNC2=NC=NC(Cl)=C12.O=C(Cl)C1=CNC2=NC=NC(Cl)=C12.O=C(O)C1=CNC2=NC=NC(Cl)=C12 Chemical compound ClC1=C2C(Br)=CNC2=NC=N1.NC(=O)C1=CNC2=NC=NC(Cl)=C12.O=C(Cl)C1=CNC2=NC=NC(Cl)=C12.O=C(O)C1=CNC2=NC=NC(Cl)=C12 OVSFACADZSVZKO-UHFFFAOYSA-N 0.000 description 1
- KKHGOSNSJFNVMK-UHFFFAOYSA-M ClC1=C2C=CNC2=NC=N1.FC1=CNC2=NC=NC(Cl)=C12.[F-] Chemical compound ClC1=C2C=CNC2=NC=N1.FC1=CNC2=NC=NC(Cl)=C12.[F-] KKHGOSNSJFNVMK-UHFFFAOYSA-M 0.000 description 1
- IIELWFVAOZBGGS-UHFFFAOYSA-N ClC1=NC=NC(Cl)=N1.N.NC1=NC(Cl)=NC=N1.O.[BH4-].[BH5-2] Chemical compound ClC1=NC=NC(Cl)=N1.N.NC1=NC(Cl)=NC=N1.O.[BH4-].[BH5-2] IIELWFVAOZBGGS-UHFFFAOYSA-N 0.000 description 1
- ZNGDPLPCVLZLLE-QGZVFWFLSA-N [C-]#[N+]C1=C(C[C@@H](C)C2=CC3=CC=CC(C4=CN(C)N=C4)=C3C(=O)N2C2=CC=CC=C2)N=CN=C1N Chemical compound [C-]#[N+]C1=C(C[C@@H](C)C2=CC3=CC=CC(C4=CN(C)N=C4)=C3C(=O)N2C2=CC=CC=C2)N=CN=C1N ZNGDPLPCVLZLLE-QGZVFWFLSA-N 0.000 description 1
- XQBCCNOZAODMHL-UHFFFAOYSA-N [C-]#[N+]CC(C)(C)C Chemical compound [C-]#[N+]CC(C)(C)C XQBCCNOZAODMHL-UHFFFAOYSA-N 0.000 description 1
- WUEMCHVIDPLPMJ-UHFFFAOYSA-N [H]C1=NC(CN(C(C)C)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(CN(C(C)C)C(C)(C)C)=C2N=CNC2=N1 WUEMCHVIDPLPMJ-UHFFFAOYSA-N 0.000 description 1
- LNPCYSYSCNYWLU-UHFFFAOYSA-N [H]C1=NC(CN(C)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(CN(C)C(C)(C)C)=C2N=CNC2=N1 LNPCYSYSCNYWLU-UHFFFAOYSA-N 0.000 description 1
- RZMBGXJFVXMGHM-UHFFFAOYSA-N [H]C1=NC(CN(CC)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(CN(CC)C(C)(C)C)=C2N=CNC2=N1 RZMBGXJFVXMGHM-UHFFFAOYSA-N 0.000 description 1
- VVOYPCDLOIJIAM-UHFFFAOYSA-N [H]C1=NC(NC(C(C)C)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(NC(C(C)C)C(C)(C)C)=C2N=CNC2=N1 VVOYPCDLOIJIAM-UHFFFAOYSA-N 0.000 description 1
- SNSSMVGKNSRPNE-UHFFFAOYSA-N [H]C1=NC(NC(C)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(NC(C)C(C)(C)C)=C2N=CNC2=N1 SNSSMVGKNSRPNE-UHFFFAOYSA-N 0.000 description 1
- SSSNFCBQFVIWFX-UHFFFAOYSA-N [H]C1=NC(NC(CC)C(C)(C)C)=C2N=CNC2=N1 Chemical compound [H]C1=NC(NC(CC)C(C)(C)C)=C2N=CNC2=N1 SSSNFCBQFVIWFX-UHFFFAOYSA-N 0.000 description 1
- ULKDSFKZLIMONF-UHFFFAOYSA-N [H]C1=NC2=C(N=CN2CC(C)(C)C)C(N)=N1 Chemical compound [H]C1=NC2=C(N=CN2CC(C)(C)C)C(N)=N1 ULKDSFKZLIMONF-UHFFFAOYSA-N 0.000 description 1
- ZPJYZWVIEXTPFK-ZETCQYMHSA-N [H]C1=NC2=C(N=CN2[C@@H](C)C(C)(C)C)C(N)=N1 Chemical compound [H]C1=NC2=C(N=CN2[C@@H](C)C(C)(C)C)C(N)=N1 ZPJYZWVIEXTPFK-ZETCQYMHSA-N 0.000 description 1
- RVCGXKXRAKWNII-UHFFFAOYSA-N [H]C1=NC2=C(OC(C)(C)C)N(C)N=C2C(N)=N1 Chemical compound [H]C1=NC2=C(OC(C)(C)C)N(C)N=C2C(N)=N1 RVCGXKXRAKWNII-UHFFFAOYSA-N 0.000 description 1
- HAKKTZOUPCDMCN-UHFFFAOYSA-N [H]N1CCC(C(C)(C)C)CC1 Chemical compound [H]N1CCC(C(C)(C)C)CC1 HAKKTZOUPCDMCN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N [H]OC(C)=O Chemical compound [H]OC(C)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
- Wa 2 is CR5 or N; Wa 3 is CR6 or N; Wa 4 is CR7 or N; wherein no more than two adjacent ring atoms selected from Wa 2,
- Wa 3, and Wa 4 are heteroatoms;
- B is hydrogen, alkyl, amino, heteroalkyl, or a moiety of formula II:
- q is an integer of 0, 1, 2, 3, or 4;
- X is absent or —(CH(R9))z—, and z is an integer of 1, 2, 3, or 4;
- Y is absent, —O—, —S—, —S(═O)—, —S(═O)2, —C(═O)—, —C(═O)(CHR9)z—, —N(R9)—, N(R9)—C(═O)—, —N(R9)—C(═O)NH—, or —N(R9)C(R9)2—, and z is an integer of 1, 2, 3, or 4;
- R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro; each R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
- R3 is cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl, alkenyl, or alkynyl, or R3 is a heteroatom selected from N, S, and O, wherein the heteroatom has a covalent bond either directly or through a C1-C6 alkyl group to an aryl, heteroaryl or heterocyclyl, or R3 and R5 are taken together with the carbons to which they are attached form a 5- or 6-membered ring; wherein each of the above substituents can be substituted with 0, 1, 2, or 3 R13;
- R5, R6, R7, and R8 are independently hydrogen, halo, cyano, alkyl or amino;
- each R9 is independently hydrogen, alkyl, or heterocycloalkyl;
- Wd is
- R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate;
- R12 is hydrogen, alkyl, haloalkyl, alkynyl, alkenyl, halo, —C(O)NH2, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl,
- Ra′ is hydrogen, alkyl, —NH2, cyano, or halogen; and
- each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, or halogen.
- B is hydrogen, alkyl, amino, heteroalkyl, or a moiety of Formula II:
- q is an integer of 0, 1, 2, 3, or 4;
- X is absent or —(CH(R9))z—, and z is an integer of 1, 2, 3, or 4;
- Y is absent, —O—, —S—, —S(═O)—, —S(═O)2, —C(═O)—, —C(═O)(CHR9)z—, —N(R9)—, N(R9)—C(═O)—, —N(R9)—C(═O)NH—, or —N(R9)C(R9)2—, and z is an integer of 1, 2, 3, or 4;
- R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro;
- each R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
- R3 is cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl, alkenyl, or alkynyl, or R3 is a heteroatom selected from N, S, and O, wherein the heteroatom has a covalent bond either directly or through a C1-C6 alkyl group to an aryl, heteroaryl or heterocyclyl, or R3 and R5 are taken together with the carbons to which they are attached form a 5- or 6-membered ring; wherein each of the above substituents can be substituted with 0, 1, 2, or 3 R13;
- R5, R6, R7, and R8 are independently hydrogen, halo, cyano, alkyl or amino;
- each R9 is independently hydrogen, alkyl, or heterocycloalkyl;
- Wd is
- R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate;
- R12 is hydrogen, alkyl, haloalkyl, alkynyl, alkenyl, halo, —C(O)NH2, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl,
- Ra′ is hydrogen, alkyl, —NH2, cyano or halogen; and
- each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy or halogen.
In some embodiments, Wc is aryl or heteroaryl. In some embodiments, Wc is 6-membered aryl (e.g., phenyl). In some embodiments, q is 0. In some embodiments, R1 is hydrogen. In some embodiments, q is 1. In some embodiments, R2 is halo (e.g., fluoro).
In some embodiments, R12 is halogen (e.g., fluoro). In some embodiments, R12 is cyano. In some embodiments, R12 is —C(O)NH2. In some embodiments, Ra′ is hydrogen.
In some embodiments, Ra′ is —NH2. In some embodiments, R12 is halo (e.g., fluoro or iodo). In some embodiments, R12 is cyano. In some embodiments, R12 is haloalkyl (e.g., trifluoromethyl).
wherein Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl; q is an integer of 0 or 1; R1 is hydrogen, alkyl, or halo; R2 is alkyl or halo; and R3 is a 5-membered heteroaryl, 6-membered heteroaryl, or fused 5/6-bicyclic heteroaryl group.
wherein Wc is aryl or cycloalkyl. In various embodiments, R3 contains one or two nitrogen atoms, with the proviso that non-nitrogen heteroatoms can be excluded. In various embodiments, R3 is a substituted or unsubstituted group selected from phenyl, pyridine, pyrazole, piperazine, imidazole and pyrrolidine. For example, the R3 group can be substituted with a C1-C6 alkyl group or a halogen.
In certain embodiments, R12 is monocyclic heteroaryl, bicyclic heteroaryl, or nonaromatic heterocyclyl. For example, R12 can be a substituted benzoxazole. In certain embodiments, R3 is a substituted or unsubstituted group selected from pyridine, pyrazole, piperazine, and pyrrolidine. The R3 group can be substituted with a C1-C6 alkyl group or a halogen.
Accordingly, in some embodiments, the compound has one stereocenter, wherein said stereocenter can be in an (S)-stereochemical configuration or an (R)-stereochemical configuration. In some embodiments, a compound is provided wherein the compound has a structure of Formula V-A2:
wherein R13 is H C1-C6 alkyl (e.g., methyl) or halo (e.g., fluoro). In some embodiments, R13 is C1-C6 alkyl (e.g., methyl). In some embodiments, R13 is halo (e.g., fluoro).
wherein R3 can be selected from pyridine, pyrazole, piperazine, and pyrrolidine; each of which can be substituted with 0, 1, 2, or 3 occurrences of R13;
- B can be a moiety of Formula II:
- Wd is selected from
ee=(90−10)/100=80%.
Thus, a composition containing 90% of one enantiomer and 10% of the other enantiomer is said to have an enantiomeric excess of 80%. Some of the compositions described herein contain an enantiomeric excess of at least about 50%, 75%, 90%, 95%, or 99% of Compound 1 (the S-enantiomer). In other words, the compositions contain an enantiomeric excess of the S enantiomer over the R enantiomer.
- Wa 2 is CR5 or N; Wa 3 is CR6 or N; Wa 4 is CR7 or N; wherein no more than two adjacent ring atoms selected from Wa 2,
- Wa 3, and Wa 4 are heteroatoms;
- B is hydrogen, alkyl, amino, heteroalkyl, or a moiety of formula II:
- q is an integer of 0, 1, 2, 3, or 4;
- X is absent or —(CH(R9))z—, and z is an integer of 1, 2, 3, or 4;
- Y is absent, —O—, —S—, —S(═O)—, —S(═O)2, —C(═O)—, —C(═O)(CHR9)z—, —N(R9)—, N(R9)—C(═O)—, —N(R9)—C(═O)NH—, or —N(R9)C(R9)2—, and z is an integer of 1, 2, 3, or 4;
- R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro; each R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
- R3 is cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl, alkenyl, or alkynyl, or R3 is a heteroatom selected from N, S, and O, wherein the heteroatom has a covalent bond either directly or through a C1-C6 alkyl group to an aryl, heteroaryl or heterocyclyl, or R3 and R5 are taken together with the carbons to which they are attached form a 5- or 6-membered ring; wherein each of the above substituents can be substituted with 0, 1, 2, or 3 R13;
- R5, R6, R7, and R8 are independently hydrogen, halo, cyano, alkyl or amino;
- each R9 is independently hydrogen, alkyl, or heterocycloalkyl;
- Wd is
- R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate;
- R12 is hydrogen, alkyl, haloalkyl, alkynyl, alkenyl, halo, —C(O)NH2, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl,
- Ra′ is hydrogen, alkyl, —NH2, cyano, or halogen; and
- each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, or halogen.
wherein Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl, and q is an integer of 0, 1, 2, 3, or 4; X is absent or —(CH(R9))z—, and z is an integer of 1, 2, 3, or 4; and Y is absent, —O—, —S—, —S(═O)—, —S(═O)2, —C(═O)—, —C(═O)(CHR9)z—, —N(R9)—, N(R9)—C(═O)—, —N(R9)—C(═O)NH—, or —N(R9)C(R9)2, and z is an integer of 1, 2, 3, or 4. In some embodiments, R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro; each R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate; and R3 is cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl, alkenyl, or alkynyl, or R3 is a heteroatom selected from N, S, and O, wherein the heteroatom has a covalent bond either directly or through a C1-C6 alkyl group to an aryl, heteroaryl or heterocyclyl, or R3 and R5 are taken together with the carbons to which they are attached form a 5- or 6-membered ring; wherein each of the above substituents can be substituted with 0, 1, 2, or 3 R13. In some embodiments, R5, R6, R7, and R8 are independently hydrogen, halo, cyano, alkyl or amino; and each R9 is independently hydrogen, alkyl, or heterocycloalkyl;
Wd is
- R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate; R12 is hydrogen, alkyl, haloalkyl, alkynyl, alkenyl, halo, —C(O)NH2, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl; Ra′ is hydrogen, alkyl, —NH2, cyano, or halogen; and each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, or halogen.
- B is hydrogen, alkyl, amino, heteroalkyl, or a moiety of Formula II:
- q is an integer of 0, 1, 2, 3, or 4;
- X is absent or —(CH(R9))z—, and z is an integer of 1, 2, 3, or 4;
- Y is absent, —O—, —S—, —S(═O)—, —S(═O)2, —C(═O)—, —C(═O)(CHR9)z—, —N(R9)—, N(R9)—C(═O)—, —N(R9)—C(═O)NH—, or —N(R9)C(R9)2—, and z is an integer of 1, 2, 3, or 4;
- R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro;
- each R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
- R3 is cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocyclyl, aralkyl, heteroaralkyl, heterocyclylalkyl, alkenyl, or alkynyl, or R3 is a heteroatom selected from N, S, and O, wherein the heteroatom has a covalent bond either directly or through a C1-C6 alkyl group to an aryl, heteroaryl or heterocyclyl, or R3 and R5 are taken together with the carbons to which they are attached form a 5- or 6-membered ring; wherein each of the above substituents can be substituted with 0, 1, 2, or 3 R13;
- R5, R6, R7, and R8 are independently hydrogen, halo, cyano, alkyl or amino;
- each R9 is independently hydrogen, alkyl, or heterocycloalkyl;
Wd is
- R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate;
- R12 is hydrogen, alkyl, haloalkyl, alkynyl, alkenyl, halo, —C(O)NH2, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl,
- Ra′ is hydrogen, alkyl, —NH2, cyano or halogen; and
- each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy or halogen.
R11 is hydrogen, alkyl, halo, amino, amido, hydroxy, alkoxy, phosphate, urea, or carbonate; R12 is H, alkyl, alkynyl, alkenyl, halo, aryl, heteroaryl, nonaromatic heterocyclyl, or cycloalkyl; Ra′ is hydrogen, alkyl, —NH2, cyano or halogen; and each R13 is independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy or halogen.
- B is alkyl, amino, heteroalkyl, cycloalkyl, heterocycloalkyl, or a moiety of Formula II:
and wherein Wc is selected from unsubstituted or substituted aryl, substituted phenyl, unsubstituted or substituted heteroaryl including, but not limited to, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, or pyrazin-2-yl, unsubstituted or substituted monocyclic heteroaryl, unsubstituted or substituted bicyclic heteroaryl, a heteroaryl comprising two heteroatoms as ring atoms, unsubstituted or substituted heteroaryl comprising a nitrogen ring atom, a heteroaryl comprising two nitrogen ring atoms, a heteroaryl comprising a nitrogen and a sulfur as ring atoms, unsubstituted or substituted heterocycloalkyl including, but not limited to, morpholinyl, tetrahydropyranyl, piperazinyl, and piperidinyl, or unsubstituted or substituted cycloalkyl including, but not limited, and cyclopentyl and cyclohexyl.
wherein R13 is H or C1-C6 alkyl. In certain embodiments, R13 is methyl. In some embodiments, R3 is selected from the following:
wherein Ra′ is hydrogen, halo, phosphate, urea, a carbonate, unsubstituted or substituted amino, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heteroalkyl, or unsubstituted or substituted heterocycloalkyl; and R12 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted cyano, unsubstituted or substituted alkynyl, unsubstituted or substituted alkenyl, halo, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted amino, carboxylic acid, unsubstituted or substituted alkoxycarbonyl, unsubstituted or substituted amido, unsubstituted or substituted acyl, or unsubstituted or substituted sulfonamido.
wherein Ra′ is hydrogen, halo, phosphate, urea, a carbonate, unsubstituted or substituted amino, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heteroalkyl, or unsubstituted or substituted heterocycloalkyl; R11 is hydrogen, unsubstituted or substituted alkyl, halo (which includes —I, —F, —Cl, or —Br), unsubstituted or substituted amino, unsubstituted or substituted amido, hydroxy, or unsubstituted or substituted alkoxy, phosphate, unsubstituted or substituted urea, or carbonate; and R12 is H, unsubstituted or substituted alkyl, unsubstituted or substituted cyano, unsubstituted or substituted alkynyl, unsubstituted or substituted alkenyl, halo, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted amino, carboxylic acid, unsubstituted or substituted alkoxycarbonyl, unsubstituted or substituted amido, unsubstituted or substituted acyl, or unsubstituted or substituted sulfonamido.
wherein R11 is H, alkyl, halo, amino, amido, hydroxy, or alkoxy, and R12 is H, alkyl, alkynyl, alkenyl, halo, aryl, heteroaryl, heterocycloalkyl, or cycloalkyl. In some embodiments, R11 is amino and R12 is H, alkyl, alkynyl, alkenyl, halo, aryl, heteroaryl, heterocycloalkyl, or cycloalkyl. In some embodiments, R11 is amino and R12 is alkyl, halo, aryl, heteroaryl, heterocycloalkyl, or cycloalkyl. In some embodiments, R11 is amino and R12 is monocyclic heteroaryl. In some embodiments, R11 is amino and R12 is bicyclic heteroaryl. In some embodiments, R11 is amino and R12 is cyano, amino, carboxylic acid, acyloxy, alkoxycarbonyl, or amido.
wherein Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl; R1 is H, —F, —Cl, —CN, —CH3, isopropyl, —CF3, —OCH3, nitro, or phosphate; R2 is halo, hydroxy, cyano, nitro, or phosphate; q is an integer of 0, 1, 2, 3, or 4; R5, R6, R7, and R8 are H; X is absent or (CH2)z; z is 1; Y is absent, —N(R9)—, or —N(R9) CH(R9)—; R9 is hydrogen, C1-C10 alkyl, C3-C7 cycloalkyl, or C2-C10heteroalkyl; and Wd is pyrazolopyrimidine or purine.
TABLE 1 |
Illustrative B moieties of compounds of Formula I |
include, but are not limited to: |
Sub-class # | B | ||
B-1 |
|
||
B-2 |
|
||
B-3 | —CH(CH3)2 | ||
B-4 |
|
||
B-5 |
|
||
B-6 |
|
||
B-7 |
|
||
B-8 |
|
||
B-9 |
|
||
B-10 |
|
||
B-11 |
|
||
B-12 |
|
||
B-13 |
|
||
B-14 |
|
||
B-15 |
|
||
B-16 |
|
||
B-17 |
|
||
B-18 |
|
||
B-19 |
|
||
B-20 |
|
||
B-21 |
|
||
B-22 |
|
||
B-23 |
|
||
B-24 |
|
||
B-25 |
|
||
B-26 |
|
||
B-27 |
|
||
B-28 |
|
||
B-29 |
|
||
B-30 |
|
||
B-31 |
|
||
B-32 |
|
||
B-33 |
|
||
B-34 |
|
||
B-35 |
|
||
B-36 |
|
||
B-37 |
|
||
B-38 |
|
||
B-39 |
|
||
B-40 |
|
||
B-41 |
|
||
B-42 |
|
||
B-43 |
|
||
B-44 |
|
||
B-45 |
|
||
B-46 |
|
||
B-47 |
|
||
B-48 |
|
||
B-49 |
|
||
B-50 |
|
||
B-51 |
|
||
B-52 |
|
||
B-53 |
|
||
B-54 |
|
||
B-55 |
|
||
B-56 |
|
||
B-57 |
|
||
B-58 |
|
||
B-59 |
|
||
B-60 |
|
||
B-61 |
|
||
B-62 |
|
||
B-63 |
|
||
B-64 |
|
||
B-65 |
|
||
B-66 |
|
||
B-67 |
|
||
B-68 |
|
||
B-69 |
|
||
B-70 |
|
||
B-71 |
|
||
B-72 |
|
||
B-73 |
|
||
B-74 |
|
||
B-75 |
|
||
B-76 |
|
||
B-77 |
|
||
B-78 |
|
||
B-79 |
|
||
B-80 |
|
||
B-81 |
|
||
B-82 |
|
||
B-83 |
|
||
B-84 |
|
||
B-85 |
|
||
B-86 |
|
||
B-87 | —CH3 | ||
B-88 | —CH2CH3 | ||
B-89 |
|
||
B-90 |
|
||
B-91 |
|
||
B-92 |
|
||
B-93 |
|
||
B-94 |
|
||
B-95 |
|
||
B-96 |
|
||
B-97 |
|
||
B-98 |
|
||
B-99 |
|
||
B-100 |
|
||
B-101 |
|
||
B-102 |
|
||
TABLE 2 |
Illustrative R12 moieties of compounds of Formula I |
include, but are not limited to: |
Sub-class # | R12 | ||
12-1 | —CN | ||
12-2 | —Br | ||
12-3 | —Cl | ||
12-4 | —CH2CH3 | ||
12-5 | —CH3 | ||
12-6 | —CH(CH3)2 | ||
12-7 |
|
||
12-8 |
|
||
12-9 |
|
||
12-10 |
|
||
12-11 |
|
||
12-12 |
|
||
12-13 |
|
||
12-14 |
|
||
12-15 |
|
||
12-16 |
|
||
12-17 |
|
||
12-18 |
|
||
12-19 |
|
||
12-20 |
|
||
12-21 |
|
||
12-22 |
|
||
12-23 |
|
||
12-24 |
|
||
12-25 |
|
||
12-26 |
|
||
12-27 |
|
||
12-28 |
|
||
12-29 |
|
||
12-30 |
|
||
12-31 |
|
||
12-32 |
|
||
12-33 |
|
||
12-34 |
|
||
12-35 | —H | ||
12-36 |
|
||
12-37 |
|
||
12-38 |
|
||
12-39 |
|
||
12-40 |
|
||
12-41 |
|
||
12-42 |
|
||
12-43 |
|
||
12-44 |
|
||
12-45 |
|
||
12-46 |
|
||
12-47 |
|
||
12-48 |
|
||
12-49 |
|
||
12-50 |
|
||
12-51 |
|
||
12-52 |
|
||
12-53 |
|
||
12-54 |
|
||
12-55 |
|
||
12-56 |
|
||
12-57 |
|
||
12-58 |
|
||
12-59 |
|
||
12-60 |
|
||
12-61 | —I | ||
12-62 |
|
||
12-63 |
|
||
12-64 |
|
||
12-65 |
|
||
12-66 |
|
||
12-67 |
|
||
12-68 |
|
||
12-69 |
|
||
12-70 |
|
||
12-71 |
|
||
12-72 |
|
||
12-73 |
|
||
12-74 |
|
||
12-75 |
|
||
12-76 |
|
||
12-77 |
|
||
12-78 |
|
||
12-79 |
|
||
12-80 |
|
||
12-81 |
|
||
12-82 |
|
||
12-83 |
|
||
12-84 |
|
||
12-85 |
|
||
12-86 |
|
||
12-87 |
|
||
12-88 |
|
||
12-89 |
|
||
12-90 |
|
||
12-91 |
|
||
12-92 |
|
||
12-93 |
|
||
12-94 |
|
||
12-95 |
|
||
12-96 |
|
||
TABLE 3 |
Illustrative X-Y-Wd of compounds of Formula I |
include, but are not limited to: |
Sub-class # | X-Y-Wd | ||
1 |
|
||
2 |
|
||
3 |
|
||
4 |
|
||
5 |
|
||
6 |
|
||
7 |
|
||
8 |
|
||
9 |
|
||
10 |
|
||
11 |
|
||
12 |
|
||
13 |
|
||
14 |
|
||
15 |
|
||
16 |
|
||
17 |
|
||
18 |
|
||
19 |
|
||
20 |
|
||
21 |
|
||
22 |
|
||
23 |
|
||
24 |
|
||
25 |
|
||
26 |
|
||
27 |
|
||
28 |
|
||
29 |
|
||
30 |
|
||
31 |
|
||
32 |
|
||
33 |
|
||
34 |
|
||
35 |
|
||
36 |
|
||
37 |
|
||
38 |
|
||
39 |
|
||
40 |
|
||
41 |
|
||
42 |
|
||
43 |
|
||
44 |
|
||
45 |
|
||
46 |
|
||
47 |
|
||
48 |
|
||
49 |
|
||
50 |
|
||
51 |
|
||
52 |
|
||
53 |
|
||
54 |
|
||
55 |
|
||
General Conditions for the Preparation of 3-(1-aminoethyl)-2-phenyl-3,4-dihydroisoquinolin-1(2H)-ones:
Isoquinoline 49 was prepared according to the following sequences: Amine 46 was prepared by Method I and converted to compound 47 using Method L. Compound 48 was then coupled to pyridin-3-ylboronic using the analogous procedure in Example 20 after which it was converted to the compound 49 according to the following procedure:
TABLE 4 |
In Vitro IC50 data for selected compounds. |
+ (greater than 10 | ++ (less than 10 | +++ (less than 1 | ||
IC50 (nM) | microMolar) | microMolar) | microMolar | ++++ (less than 100 nM) |
PI3K δ | Compound No. | Compound No. | Compound No. | Compound No. |
4, 17, 50, 54, | 5, 29, 30, 34, 39, 40 | 6, 7, 9, 12, 13, 16, 18, | ||
19, 20, 21, 8, 25, 27, | ||||
31, 33, 36, 37, 38, | ||||
56, 41, 58, 45, 49, 52, | ||||
62, 67, 68, 65, 69, 72, | ||||
73, 74, 76 | ||||
PI3K γ | Compound No. | Compound No. | Compound No. | Compound No. |
5, 50, 54 | 4, 17, 29, 30, 31, 33, | 6, 20, 39, 49, 52, 62, | 7, 9, 12, 13, 16, 18, | |
34, 40, 76 | 74 | 19, 21, 8, 25, 27, 36, | ||
37, 38, 56, 41, 58, 45, | ||||
67, 68, 65, 69, 72, 73 | ||||
PI3K α | Compound No. | Compound No. | Compound No. | Compound No. |
4, 5, 16, 17, 18, 19, | 6, 7, 9, 13, 20, 21, 8, | 12, 349, 36, 37, 38, | ||
29, 30, 31, 33, 34, 39, | 25, 27, 58, 45, 52, 62, | 56, 41 | ||
40, 49, 50, 54, 67, 68, | 72, 73, 76 | |||
65, 69, 74 | ||||
PI3K β | Compound No. | Compound No. | Compound No. | Compound No. |
4, 5, 6, 17, 18, 19, 27, | 7, 9, 16, 20, 21, 8, 25, | 12, 13, 349 | 72 | |
29, 30, 31, 33, 34, 39, | 36, 37, 38, 56, 41, 58, | |||
40, 45, 49, 52, 50, 54, | 62 | |||
67, 68, 65, 69, 73, 74, | ||||
76 | ||||
B cell proliferation | Compound No. | Compound No. | Compound No. | Compound No. |
EC50 (nM) | 4, 29, 30, 34 | 5, 6, 7, 9, 12, 13, 16, | ||
17, 18, 19, 20, 21, 8, | ||||
25, 27, 31, 33, 36, 37, | ||||
56, 41, 45, 49, 52, 62, | ||||
67, 68 | ||||
TABLE 5 |
Structures of the Compounds for the IC50 results described in Table 4. |
Structure | |
|
Compound 4 |
|
Compound 5 |
|
Compound 6 |
|
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Compound 30 |
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Compound 38 |
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Compound 56 |
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Compound 39 |
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Compound 58 |
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Compound 45 |
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Compound 49 |
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Compound 52 |
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Compound 50 |
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Compound 54 |
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Compound 60 |
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Compound 67 |
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Compound 68 |
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Compound 65 |
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Compound 69 |
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Compound 73 |
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Compound 72 |
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Compound 74 |
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Compound 76 |
Claims (30)
Priority Applications (1)
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